US2525898A - 1, 3-diphenylimidazolidine and certain derivatives thereof used as acid fading inhibitors - Google Patents

1, 3-diphenylimidazolidine and certain derivatives thereof used as acid fading inhibitors Download PDF

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Publication number
US2525898A
US2525898A US778749A US77874947A US2525898A US 2525898 A US2525898 A US 2525898A US 778749 A US778749 A US 778749A US 77874947 A US77874947 A US 77874947A US 2525898 A US2525898 A US 2525898A
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United States
Prior art keywords
acid
cellulose
fading
water
colorations
Prior art date
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Expired - Lifetime
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US778749A
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English (en)
Inventor
Grimmel Harry Wilhelm
Guenther Alfred
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GAF Chemicals Corp
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General Aniline and Film Corp
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Filing date
Publication date
Priority to BE484907D priority Critical patent/BE484907A/xx
Application filed by General Aniline and Film Corp filed Critical General Aniline and Film Corp
Priority to US778749A priority patent/US2525898A/en
Priority to GB21426/48A priority patent/GB648651A/en
Priority to FR988496D priority patent/FR988496A/fr
Application granted granted Critical
Publication of US2525898A publication Critical patent/US2525898A/en
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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
    • D06P1/642—Compounds containing nitrogen
    • D06P1/6426—Heterocyclic compounds

Definitions

  • an acid fading inhibitor shduld 'bel-coljorless adapted to withstand prolonged exposure to light and/or combustion. gases without discoloration, fast to. dry-cleaning and wetew smsg, odorlesaand non toxic in the sense that it causesno skin irritations when materials treated therewith are worn. whilemost of the acid fading inhibitorsheretofore proposed satisfy anuinber .of theserequirements, in, most cases Many, of the. proposed materials are toolsoluble 12 Claims. (01. 8--61) Water or in dry-cleaning solvents so that they are largely removed when textile materials treated therewith are subjected to customary cleansing treatments.
  • the acid fading inhibitors be applicable to the goods to be dyed together'with the dyestuff, so that a separate pie-treatment or after-treatment can beavpided.
  • the.compounds employed must have suitable solubility properties, e. g., they should be insoluble but dispersible in water, ,and should possess a natural affinity for organic derivatives of cellulose.
  • the compounds employed have a sufiiciently high melting point to avoid fusion in the dye bath.
  • the molten compound forms an oil which generally separates from the dispersion and dissolves a substantial ,portionlof the dispersedwater-insoluble dyestuff.
  • the resultingliquidoil-dye mixture is generally deposited ,on the ugoodstobe dyed, forming unsightly spots or streaks. While many of the disclosures in-the p ior art of acid fading. inhibitors indicate that they can be applied t oltextile materials at any time during the processing thereof, including.
  • the acid fading inhibitors of this invention are represented by the general formula CH2CH2 X Y OH/ wherein X and Y are nuclear substituents selected from the group consisting of hydrogen and non-solubilizing groups and radicals (e. g., alkyl, halogen, nitro, and cyano groups), and R is selected from the group consisting of hydrogen, alkyl, aryl, and heterocyclic radicals which are free of solubilizing substituents.
  • X and Y are nuclear substituents selected from the group consisting of hydrogen and non-solubilizing groups and radicals (e. g., alkyl, halogen, nitro, and cyano groups)
  • R is selected from the group consisting of hydrogen, alkyl, aryl, and heterocyclic radicals which are free of solubilizing substituents.
  • 1,2,3- triphenylimidazolidine can be prepared by heating benzaldehyde with NNdiphenyl-ethylenediamine to boiling
  • the resulting imidazole derivative can be purified by recrystallization from alcohol, petroleum ether, benzene or other suitable solvents.
  • 2-methyl-1,3-diphenylimidazolidine can be prepared in an analogous manner by substituting acetaldehyde for benzaldehyde in the aforesaid procedure, and Z-furyl- 1,3-ditolylimidazolidine can be similarly prepared from furfural and NN-ditolyl-ethylenediamine.
  • taining organic derivatives of cellulose from a dye-bath together with the dyestuff.
  • they are colorless, are notv discoloredon .prolonged exposure to light or combustion gases, are insoluble in water, and fast to dry-'cleam'ngof the textile materials with the usual dry-cleaningv solvents, so that they withstand the. effects of usual cleaning operations of materials in which they are incorporated without loss of their effectiveness.
  • they are odorless and nonirritating to the skin when incorporated in textile materials.
  • they can be readily dispersed in water in the same manner as is usual for dyestuffs employed for coloring organic celluganic derivatives of cellulose.
  • the inhibitors of this invention can be dis-' persed in the aqueous bath by any of the methods commonly used for similar, dispersion of water-insoluble dyestuffs adapted for dyeing or For instance, they may be dissolved together with the dyestuff in a water-miscible solvent, and brought into dispersion by addition of a concentrated aqueous solution of a dispersing agent having soap-like properties and/or protective colloid action, whereupon the resulting mixture can be diluted with sufficient water to yield a dye bath of the desired concentration.
  • the amount of acid fading inhibitor of our invention which can be employed may be varied within rather wide limits. Thus, we have found them to be fully effective in amounts corresponding to about 1% by weight of the quantity of organic derivative of cellulose subjected to treatment therewith, and can be applied from a dyebath or treatment bath containing said compounds in concentrations from 0.01 to 0.1%, such amounts being, for example, of the order of lto 5 times the amount of dyestuif employed.
  • Example I l to 2 parts of 2-methy1-1,3-diphenylimidazolia dine and 0.6 part of a blue cellulose acetate dye consisting essentially of l-(2-hydroXy-ethylamino) 4 (monoinethylamino) anthraqui none are dissolved in a small quantity of a sol,- vent composed of equal proportions ofalcohol and acetone (or another suitable water-miscible solvent), and 40-parts of a 5% aqueous solution of N,N-oleyl-methyltaurine sodium salt, or of another suitable saponaceous dispersing agent, are added to the aforesaid solution; The resulting mixture is diluted with 5000 parts of warm One hunf dred parts of cellulose acetate silk in the form of yarn or fabric is immersed in the dye-bath, the temperature gradually raised 1 to -90 0., and
  • ErampZe II 1 to 2 parts of .Z-furyle1,3-ditolylimidazolidine are dissolved, as in the preceding example, in a mixture of equal parts of alcohol. and acetone,
  • Cellulosehacetateg materials dyed with other dyestufis; particularly those of the blue range, can be treated inthe same manner as in the. foregoing example, and other 1,3-diphenylimidazolidines can be employed instead of the 2-furyl- 1,3 ditolylimidazolidine of the example, with similarly advantageous rsults.
  • Example II can be applied to undyed textile materials containing organic derivatives of cellulose, before carrying out a dyein operation thereon in order to render the resulting coloration fast to acid fumes.
  • the acid fading inhibitors of this invention can be applied singly,.or combinations of two or more inhibitors can be used.
  • Textile material comprising dyed fibers 'of an organic derivative of cellulose dyed with a water-insoluble .dyestuff yielding colorations on said fibers normally subject to fading when exposed to acid fumes, having incorporated in said fibers a colorless water-insoluble 1,3-diphenylimidazolidine having the general formula x onhom Y ⁇ CH/ wherein X and Y are nuclear substituents selected from the group consisting of hydrogen, alkyl,
  • R is' selected from the group consisting of hydrogen, alkyl, iaryl, and furyl radicals which are free of solubilizin substituents.
  • Textile material comprising dyed fibers of an organic derivative of cellulose dyed With a water-insoluble dyestuif yielding colorations on said fibers normally subject to fading when exposed to acid fumes, having incorporated in said fibers Z-furyl-1,3-ditolylimidazolidine.
  • a colorless water-insoluble 1,3-diphenylimidazolidine having the general formula wherein X and Y are nuclear substituents selected from the group consisting of hydrogen, alkyl, halo, nitro and cyano groups, and R is selected from the group consisting of hydrogen, alkyl, aryl, and furyl radicals which are free of solubilizing substituents, in a dye-bath containing a water-insoluble dyestuff for said organic derivative of cellulose, yielding colorations thereon which are normally subject to fading when ex-' posed to acid fumes, and working said material in the resulting bath until dyeing is-complete.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)
US778749A 1947-10-09 1947-10-09 1, 3-diphenylimidazolidine and certain derivatives thereof used as acid fading inhibitors Expired - Lifetime US2525898A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
BE484907D BE484907A (de) 1947-10-09
US778749A US2525898A (en) 1947-10-09 1947-10-09 1, 3-diphenylimidazolidine and certain derivatives thereof used as acid fading inhibitors
GB21426/48A GB648651A (en) 1947-10-09 1948-08-13 Treatment of cellulose esters and ethers with imidazolidine derivatives to inhibit gas fading
FR988496D FR988496A (fr) 1947-10-09 1948-09-02 Perfectionnement au traitement de matières cellulosiques en vue d'augmenter la solidité des couleurs appliquées sur ces matières

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US778749A US2525898A (en) 1947-10-09 1947-10-09 1, 3-diphenylimidazolidine and certain derivatives thereof used as acid fading inhibitors

Publications (1)

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US2525898A true US2525898A (en) 1950-10-17

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US (1) US2525898A (de)
BE (1) BE484907A (de)
FR (1) FR988496A (de)
GB (1) GB648651A (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2762680A (en) * 1952-10-02 1956-09-11 Celanese Corp Production of inhibitor gel compositions

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4208182A (en) * 1976-02-17 1980-06-17 Toyo Ink Manufacturing Co., Ltd. Process for transfer printing at elevated temperatures

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1930232A (en) * 1929-06-25 1933-10-10 Celanese Corp Coloration of materials
US2083122A (en) * 1932-07-19 1937-06-08 Celanese Corp Manufacture of artificial filaments, threads, films, and the like
US2148655A (en) * 1937-09-29 1939-02-28 Celanese Corp Coloration of textile materials
US2176506A (en) * 1938-03-14 1939-10-17 Eastman Kodak Co Treatment of textile and other materials
US2255090A (en) * 1940-02-13 1941-09-09 Du Pont Inhibiting the gas fading of dyed acetate silk
US2298401A (en) * 1940-08-22 1942-10-13 Eastman Kodak Co Treatment of textile material
US2340375A (en) * 1940-09-02 1944-02-01 Ici Ltd Treatment of cellulose esters and ethers
US2416380A (en) * 1942-07-18 1947-02-25 Ici Ltd Inhibition of acid-fading on dyed cellulose acetate with n:n' diphenylethylene diamine

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1930232A (en) * 1929-06-25 1933-10-10 Celanese Corp Coloration of materials
US2083122A (en) * 1932-07-19 1937-06-08 Celanese Corp Manufacture of artificial filaments, threads, films, and the like
US2148655A (en) * 1937-09-29 1939-02-28 Celanese Corp Coloration of textile materials
US2176506A (en) * 1938-03-14 1939-10-17 Eastman Kodak Co Treatment of textile and other materials
US2255090A (en) * 1940-02-13 1941-09-09 Du Pont Inhibiting the gas fading of dyed acetate silk
US2298401A (en) * 1940-08-22 1942-10-13 Eastman Kodak Co Treatment of textile material
US2340375A (en) * 1940-09-02 1944-02-01 Ici Ltd Treatment of cellulose esters and ethers
US2416380A (en) * 1942-07-18 1947-02-25 Ici Ltd Inhibition of acid-fading on dyed cellulose acetate with n:n' diphenylethylene diamine

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2762680A (en) * 1952-10-02 1956-09-11 Celanese Corp Production of inhibitor gel compositions

Also Published As

Publication number Publication date
FR988496A (fr) 1951-08-28
BE484907A (de)
GB648651A (en) 1951-01-10

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